When he was asked to name the three most important virtues, Augustine replied: “humility, humility, and humility” (Ep. 118.22). How did he come to that ringing statement? The answer: the hard way. Humility was not a natural attitude for Augustine, who to me comes across as an alpha male who always had to be the center of attention. Peter Brown said it was hard to be in his circle because “Augustine was an imperialist in his friendships.”

Once Augustine had gotten his act together in his early 30s, he turned to helping others realize how humility had been a lifesaving virtue. Right after he’d stepped off his career ladder, he and a few friends along with his mother Monica were living in a comfortable country retreat in northern Italy not far from Lake Como. He wrote a short dialogue called On the Happy Life from this villa. He described the vice of pride as a huge mountain that stands in the way of contentment, joy, and personal fulfillment. That mountain, he advises from personal experience, “must be very seriously feared and carefully avoided.” The mountain is an obstacle that dazzles you with its light and height. Beware its siren song enticing you to climb “the proud pursuit of empty glory.” That climb will only cast you down, “for within there is nothing substantial or solid and, with a cracking of the ground-crust beneath, it collapses and swallows up those walking above, puffed up with themselves, and, as they tumble headlong into darkness, it withdraws from them the gleaming dwelling place just barely seen” (De beata vita, 3). Having fallen through his own pride, Augustine warns his readers to avoid this lethal bait-and-switch.

To his credit, in Confessions Augustine extensively offered himself up as Exhibit A of what a life driven by pride looks like. Augustine indicts his younger self as ambitious, obnoxious, greedy, always acting with uncontrolled emotions and sexual desires, and constantly unsatisfied by answers that settled matters for others but never fully for him. He described himself there as a restless, searching, and arrogant young man who was always on the move and on the make. D. J. Macqueen concluded that Augustine “exhibited an almost morbid and constantly increasing preoccupation with pride viewed as a major personal problem.” He admits he loved being popular, praised, and prized. He knows that he was (and you get the sense that he still is at that point) self-absorbed. If he didn’t understand a concept, it was the concept’s fault. He was stubborn and willful. Augustine was sure he could prosper on his own merits, yet still he emotionally always needed to be surrounded by people telling him how great he was. But Augustine didn’t require them to fill him with hot air (though he sounds like he didn’t mind); he did that just fine by himself.

Over time, he learned how wrong he was. In one episode, he recounts in Confessions that he was reading the Bible as a student of rhetoric and decided that it didn’t measure up to the Greco-Roman philosophy and classical literary style he’d been studying and imitating. But looking back from his own middle age of forty-seven, he sees now that he was simply arrogant when he made that presumptuous judgment. “It was enfolded in mysteries, and I was not the kind of man to enter into it or bow my head to follow where it led. But these were not the feelings I had when I first read the Scriptures. To me they seemed quite unworthy of comparison with the stately prose of Cicero, because I had too much conceit to accept their simplicity and not enough insight to penetrate their depths. It is surely true that as the child grows these books grow with him. But I was too proud to call myself a child. I was inflated with self-esteem, which made me think myself a great man” (Conf., III.5).

Success in rhetoric led Augustine to take up the study of law, where he shamelessly chased ambition and status. “The more unscrupulous I was,” he reports in Confessions, “the greater my reputation was likely to be, for men are so blind that they even take pride in their blindness.” At least he’s honest enough to realize now that he was proud of his pride then: “I was pleased with my superior status and swollen with conceit” (Conf. III.3). But he came to realize that as a student he didn’t understand Socrates’ fundamental lesson in the humility of learning: inflated with pride and a self-possessed sense of his own importance, he didn’t know what he didn’t know. Augustine was that worst of students in any age: the ones who tell teachers they’re already more expert than their instructors about a particular topic—which often makes professors wonder: then why are you taking this course in the first place? When you already have all the answers, who needs questions? When you are certain, what’s the point of doubt?

Once he became bishop of Hippo, Augustine turned his rhetorical skills to preaching and teaching. There is always the maddening sense, however, that he’s still pretty sure he’s right and everyone else is wrong, even as he recommends humility to counter pride. Sometimes it sounds as if he’s checking himself—or maybe he’s still clueless. In the letter where he recommended humility as the three prime virtues, Augustine was responding to a Greek man studying in north Africa named Dioscurus. He reminds us of Augustine in his youth. Dioscurus is in a hurry because he’s about to set sail on a trip and had written obnoxiously to Augustine requesting quick replies to questions about Cicero so he would appear learned to others.

You can almost hear Augustine sighing as he hears his own young self in Dioscurus’ impatient letter. And yet, he starts his reply with a degree of haughtiness by chastising this man. Doesn’t Dioscurus realize that a bishop like Augustine is far too busy to deal with such an impertinent request from someone lower than a man of his importance, learning, and tight schedule? “For when I consider how a bishop is distracted and overwrought by the cares of his office clamoring on every side, it does not seem to me proper for him suddenly, as if deaf, to withdraw himself from all these, and devote himself to the work of expounding to a single student some unimportant questions in the Dialogues of Cicero.” He counsels Dioscurus to slow down “because, unless humility precede, accompany, and follow every good action which we perform, being at once the object which we keep before our eyes, the support to which we cling, and the monitor by which we are restrained, pride wrests wholly from our hand any good work on which we are congratulating ourselves” (Ep. 118.2-3, 23).

For Augustine, pride and not money is the root of all evil. The antidote is humility, which deflates ambition and a swollen ego which put you above everyone else. Because of pride, there is no humility. You’re convinced that you can’t be wrong, which makes Augustine infuriating. Once he became convinced that his pursuit of fame and money was wrong, he was just as sure that his new path was correct and that now he was right about everything again, like the far-left liberal who shoots to the other end of the political spectrum and becomes a far-right conservative. As we just saw, Augustine didn’t always practice what he preached. In one sermon he proclaimed, “The sum of humility for you consists in knowing yourself,” which prompts Augustine and us to recall that humility can easily slip through your fingers even after it’s embraced.

This essay is adapted from Christopher M. Bellitto’s recent book, Humility: The Secret History of a Lost Virtue (Georgetown University Press, 2023).